Jon Lester Rumors

The Dodgers are reportedly willing to pay half of Andre Ethier‘s salary in a trade, but it’s still hard to figure out where he might be able to find regular playing time, Eno Sarris of Fangraphs writes. Ethier is nearly 33 and profiles as a below-average player, and half of the $56MM remaining on his contract is still more than he would likely get on the open market. The Braves are one team who could conceivably use him. The Phillies might work if Ethier weren’t left-handed, and the Rangers could make sense if they didn’t already have so many corner outfield options. Overall, though, there shouldn’t be much of a market. Here’s more from the National League.

Top Pirates prospect Jameson Taillon is scheduled to face live batters next week for the first time since undergoing Tommy John surgery in April, Travis Sawchik of the Pittsburgh Tribune-Review writes. Taillon, the No. 2 overall pick in the 2010 draft, only has six career starts at Triple-A, and the Pirates tend to be cautious about promoting their prospects. Health permitting, though, he could make his big-league debut at some point in the second half of the season.

The signing of Jon Lester helped change the Cubs‘ reputation, Paul Sullivan of the Boston Herald writes. The Cubs will lean heavily on young players this season, but Lester says there’s no reason not to expect those players to win right out of the gate. “Time to grow up sometime,” says Lester. “When I played in Boston we didn’t have time to grow up. You just had to show up and play, and each year you’re expected to win.”

We learned last night that the market for James Shields was taking shape, with multiple offers on the table and an expectation that the righty would be signed by the end of the week. Today figures to deliver plenty more reporting on the best remaining free agent, and we’ll keep tabs on it here.

The Cubs have entered the fray and are “kicking the tires” on Shields, reports David Kaplan of CSNChicago.com. Kaplan, too, hears that Shields is expected to choose a team by the end of the week, and the Cubs are among those he is considering. Kaplan tweets that the Cubs have been waiting to see where the Shields market ended up before getting too involved. He adds that Shields has interest in Chicago, with his relationship with manager Joe Maddon being a factor.

Earlier Updates

Shields’s agent, Page Odle, has indicated to some clubs that his client is “getting close to resolution,” according to ESPN.com’s Buster Olney (via Twitter).

While it remains unclear exactly where they stand, the Marlins “remain in talks” involving Shields, MLB.com’s Joe Frisaro reports. As he writes, the club is more interested in a three-year deal than in going to four, with its pursuit complicated by payroll projections and the undecided situation of Dan Haren.

If Miami is in, several other at-least-hypothetical landing spots appear to be out: The Cardinals prefer to plug Carlos Martinez in the rotation rather than signing Shields, tweets Derrick Goold of the St. Louis Post-Dispatch. The Rangers have not modified their intentions to avoid major free agent pitching investments, according to MLB.com’s T.R. Sullivan (via Twitter). And the always-unpredictable Athletics are not involved, per a tweet from Heyman.

Two more west coast teams, the Giants and Angels, are also not currently in the running, Heyman reports (Twitterlinks). San Francisco had been in conversations in the four-year, $80MM range with Shields earlier in the offseason, per an Olney tweet, but ended up pursuing (and signing) Jake Peavy and Ryan Vogelsong when they were rebuffed.

As things stand, the Nationals have the game’s best rotation while the Royals have the top pen, ESPN.com’s Buster Olney opines (Insider links). Of course, the offseason is not yet over. Here are the latest notes on the pitching market:

Diamondbacks GM Dave Stewart confirmed that the team has active interest in starter James Shields, Joel Sherman of the New York Post reports on Twitter. Stewart adds that he likes the idea of Shields serving as a mentor while fronting the team’s rotation. Fellow free agent Max Scherzer, however, is too spendy for Arizona.

When the Cardinals pursued lefty Jon Lester, the team indicated it was willing to spend only to the $120MM range, Olney tweets. That could give an idea of what kind of payroll space the club feels willing to occupy, says Olney. St. Louis was recently linked to a trio of top starting pitchers, each of whom would represent quite a different investment.

Alexi Ogando apparently produced solid results in his recent workout, with Peter Gammons of GammonsDaily.com tweeting that scouts were impressed. The Red Sox and Dodgers are “aggressive” on Ogando, Gammons adds. Nick Cafardo of the Boston Globe had tweeted that Boston was in attendance.

Righty Matt Albers is throwing in preparation for a showcase early next month, Jon Morosi of FOX Sports reports (Twitterlinks). The shoulder issues that shut him down last year did not involve any structural damage, says Morosi.

Agent Bobby Witt says that client Scott Baker, another free agent righty, prefers to join a team that will allow him to enter camp as a starter, Morosi reports (Twitterlinks). Baker has five minor league offers in hand but is hoping to receive a major league contract.

Interest in lefty Phil Coke is “amping up,” Chris Iott of MLive.com tweets. Nevertheless, a signing does not appear to be imminent, per the report.

The Twins are planning to watch lefty Johan Santana throw today after already seeing him on the mound last week, Darren Wolfson of 1500 ESPN tweets. Santana is not the only prominent hurler eyeing a comeback, it seems. Former closer Carlos Marmol threw in the Dominican earlier this winter and is now pitching in Venezuela, Jon Heyman of CBSSports.com tweets. And one-time relief ace Daniel Bard, whose career derailed with a failed conversion back to the rotation, is also seeking a return, Cafardo reports. The 29-year-old says he is finally healthy and expects to sign a deal this week.

After covering some Orioles Notes and Rays Notes earlier tonight, let’s look elsewhere around the American League East…

Cubs southpaw Jon Lester discussed a number of topics during a radio interview on WEEI’s Hot Stove Show, including the extension negotiations that took place between he and the Red Sox last spring. When asked if he would’ve accepted an extension in the range of five years and $120MM, Lester said, “That is one of those deals where hindsight is 20/20. You go back in time and you look at it and you go probably yes. I mean you don’t know. I mean it is one of those deals where when it is sitting in front of you that is a lot of money to turn down. That would have made it very difficult to turn it down.” Boston instead opened talks with a below-market four-year/$70MM offer that seemed to be the first step towards Lester eventually leaving the club. (Hat tip to WEEI.com’s Ryan Hannable for the partial transcript of Lester’s comments.)

The Red Sox highly value Brock Holt and have little interest in trading him, two sources tell MassLive.com’s Jason Mastrodonato. Holt’s versatility makes him a very important bench piece for Boston, and the team isn’t likely to deal the utilityman unless they receive an offer too good to refuse.

The Yankees may not be done adding bullpen pieces, but they’re apparently not interested in righty Jason Grilli, George A. King III of the New York Post reports. Gary Sheffield, Grilli’s agent, tells King that “We talked to Cash [Brian Cashman], and he said ‘not at the moment.’ We will sit back with the offers we have and wait.”

In another piece from George A. King III, Yankees president Randy Levine seemed to rule out the possibility that his team will sign Max Scherzer, without mentioning the free agent righty by name. “We are out there looking [for pitching], but it has to be tempered by the reality of the organization. Looking at our pitching staff, for example, we have two guys with a lot of money and we have to build around that,” Levine said. “The chances of us bringing in a guy for six [years] and $25 million [per year] or over in my opinion is virtually none. At the end of the day, you have to be realistic in any organization.” While James Shields, another top-tier free agent ace, isn’t expected to receive a deal in the six-year/$25MM average annual value range, King thinks Shields could also be out of the Yankees’ price range.

DEC. 16: Jon Heyman of CBS Sports tweets the breakdown of the deal: $15MM of the signing bonus is payable on April 1 of the coming year, with the other $15MM apparently being spread out over the life of the deal. Lester will then earn $15MM in 2015, $20MM in 2016-17, $22.5MM in 2018-19 and $15MM in 2020.

DEC. 13: The Cubs have announced that they’ve signed former Red Sox and Athletics ace Jon Lester, with a press conference scheduled for Monday. Lester will receive six years and $155MM. The deal also includes a $25MM option for a seventh year with a $10MM buyout, with the option vesting if Lester pitches 200 innings in 2020 or 400 total innings in 2019 and 2020. The deal includes a $30MM bonus, of which Lester will receive $20MM up front and another $10MM spread over the life of the contract. Lester will receive a full no-trade clause. The annual salary breakdown of the deal remains unreported.

The Red Sox’ final bid for the ACES client was six years and $135MM, according to Yahoo! Sports’ Jeff Passan (on Twitter). It emerged last week that the Giants and Dodgers were no longer contenders to sign Lester.

“It feels like we’ve definitely won the baseball lottery,” said new Cubs manager Joe Maddon upon learning of the Lester news, according to New York Daily News’ Andy Martino (via Twitter).

Lester’s free agent status seemed to be holding up a congested pitching market, but for as long as it took for Lester to agree to terms, the six years and $155MM he will receive is about what should have been expected — MLBTR’s Steve Adams predicted last month that Lester would receive a six-year, $153MM deal. The contract will make Lester one of baseball’s richest pitchers, with an AAV of $25.8MM that ranks just ahead of Justin Verlander‘s $25.7MM and behind only Clayton Kershaw‘s $30.7MM.

In Chicago, Lester will front the rotation of an emerging Cubs team that was on the lookout for top-level pitching to complement their outstanding core of young hitting. The Cubs had agreed to terms with fellow starting pitcher Jason Hammel earlier this week, and they’ve also added Maddon and catcher Miguel Montero this offseason.

The Red Sox, meanwhile, will likely continue to look for top pitching (perhaps turning to another top free agent hurler like James Shields, or to a trade target like Cole Hamels or Jordan Zimmermann) after losing out on their former ace. If they don’t, they could become a target of second-guessing after reportedly proposing a $70MM extension offer to Lester last spring.

Lester, 30, bolstered his free-agent status with an exceptional 2014 season, posting a 2.46 ERA, 9.0 K/9 and 2.0 BB/9 in 219 2/3 innings. He was strong in 21 starts for Boston and didn’t miss a beat after the Red Sox traded him and Jonny Gomes to Oakland for Yoenis Cespedes and a competitive balance pick. Since Lester was traded in-season, he could not be extended a qualifying offer and thus will not cost the Cubs a draft pick.

FOX Sports’ Ken Rosenthal was the first to tweet that the two sides had agreed to terms. Jeff Passan of Yahoo! Sports reported that the deal was for six years and $155MM. Jayson Stark of ESPN.com reported various aspects of the terms of the contract (linkstoTwitter), and CSN Chicago’s David Kaplan reported that the deal contained a $15MM vesting option. Passan added detail on the terms of Lester’s bonus.

“It’s not every day the best free agent goes to a team that finished in last place,” Cubs President of Baseball Operations Theo Epstein said today at the press conference announcing starting pitcher Jon Lester‘s new six-year contract. Epstein later explained, “We knew early on that if we signed Jon Lester, it would be about belief. It was because he would believe in us, believe in our future, and believe that winning a World Series with the Cubs was a unique opportunity.”

According to Epstein, the ability to contend for Lester’s services was a culmination of “a pretty quick rebuild” due to the hard work of the Cubs’ scouting and player development people. The Cubs now possess a trove of young position player talent, including Anthony Rizzo, Starlin Castro, Jorge Soler, Kris Bryant, Javier Baez, Addison Russell, and Kyle Schwarber. Epstein considers the Lester signing a transition to a point where the team is “clearly very serious about winning a World Series.” Lester agreed, telling the crowd,“I can tell you honestly, I wouldn’t be here if I didn’t think they were going to win in 2015.”

Lester said the chance of winning a World Series with a team that hasn’t done so since 1908 “just adds that little extra for me.” Questioned on the topic later, Epstein admitted the team’s long history of losing actually helped them sign Lester. “We’re not hiding the ball. The fact that we haven’t won in so long helps define who we are. It adds meaning and resonance to what we’re trying to accomplish here, and I think it attracts players who aren’t afraid of that challenge and want to be here for the right reasons and it definitely attracted Jon Lester.”

The Cubs’ front office and ownership gave Lester the largest contract in franchise history, a reported $155MM deal with a seventh-year vesting option and a full no-trade clause. It didn’t take long for Epstein to concede to the no-trade clause, a rarity for him. “I don’t usually like those, but when you’re talking about a free agent of this caliber who had just gotten traded to Oakland as a result of having a team that relied on some young players and ended up with a disappointing performance, it would have been really hard to sign him without a no-trade given the unique circumstances involved here. In the spirit of the negotiation, it was something that we initially objected to but didn’t keep the fight up too long because it was outside the spirit of the connection that we were trying to make.”

Epstein went up against his and Lester’s former employer, the Red Sox, in negotiations that went down to the wire at the Winter Meetings in San Diego. The Red Sox topped out at a reported $135MM offer, though they didn’t help their cause four months earlier by trading Lester, Jonny Gomes, and cash to the Athletics for Yoenis Cespedes and a competitive balance pick. When Bob Nightengale of USA Today asked Lester whether it would have been a lot harder to leave Boston had he not been traded, the lefty replied, “Yeah, I think so. I think there’s always that unknown when you are traded. Obviously that’s the unknown of going to a whole different coast, a whole different organization, a whole different philosophy. I think going there prepared us for this time. I think if you finish out the year in Boston and you get down to this decision, I think it would be a lot harder. Not to say it wasn’t hard as it was. But I feel like that broke that barrier of, ‘Well, I wonder if I can play for another team.’ And I think we answered those questions.”

Though Lester’s deal with the Cubs was consummated at last week’s Winter Meetings, it was the product of more than a month’s worth of courting. The Cubs sent Lester a 15-minute video on the first day of free agency, talking about the team’s future. Epstein and company experienced a turning point in a mid-November meeting, after which they felt “unmistakable momentum.” That momentum never waned, even through tense late night negotiations with Lester’s agents at ACES.

For his part, Lester said he enjoyed initial meetings with teams, but the second phase of actually making a decision was not fun. Much has been made of Lester’s long relationship with Epstein and Cubs GM Jed Hoyer, dating back to the pitcher being drafted out of high school in ’02. Both sides agreed that the comfort level and trust helped.

Does the Lester signing mean the Cubs are all-in for 2015? As Epstein described it, “We’re very much all-in for our future, and the future starts in 2015.” Asked whether the team is interested in trade targets with only one year of remaining control, Epstein answered, “Yeah, if they were priced accordingly. Obviously those players carry less value in our minds than players you can control going forward.”

The Cubs have already spent almost $180MM on free agents Lester, Jason Hammel, Jason Motte, and Tsuyoshi Wada, and they also traded for Tommy La Stella and well-paid catcher Miguel Montero. I talked to Hoyer about remaining potential areas for upgrade, and he said the Cubs may attempt to add an outfield bat, given the youth of the team’s current group. Asked if there’s room for another starting pitcher, Hoyer replied, “Potentially. We’re not going to sit here and say we’re done. I think we’re very comfortable going forward right now with what we have, but obviously the winter’s not over yet, there’s a lot of guys out there and we’ll certainly be engaged on some of those guys.”

The Epstein rebuild has taken three years to reach this point, and the team’s president said today that the Cubs’ “incredibly patient” fans “truly deserve a pitcher and a person of this caliber to call their own.” Lofty expectations have been set for Lester, who appears ready for the challenge.

Red Sox president and CEO Larry Lucchino didn’t mince words today about the team’s failure to sign Jon Lester, John Tomase of the Boston Herald writes. “We didn’t succeed, so I don’t give us a very good grade,” said Lucchino. “We were trying, sincerely, to get him signed, and wanted him to come back here, but free agency is a special opportunity for a player, and it only comes up once or twice if you’re lucky in your career.” Lucchino again characterized the Red Sox’ $70MM extension offer from the spring — widely perceived to be an attempt to lowball Lester — as just a starting point for negotiations, but noted that offer didn’t create the dialogue the Red Sox hoped for. Lucchino said that the Red Sox’ $135MM offer was sincere, and that they would have been happy had he accepted.

Nats exec Mike Rizzo says he’s striking a “delicate balance” between winning now and winning in the future, Chelsea Janes of the Washington Post writes. Nonetheless, perhaps unsurprisingly, it sounds like the Nationals are going to take another serious shot at winning in 2015, despite the possible departures of so many core players after the season. “We have a good team we know that can compete to play meaningful games in October. We’re going to take that and run with it,” says Rizzo.

Jason Hammel and Jeff Samardzija both helped their former Athletics teammate Jon Lester in his decision to sign with the Cubs, MLB.com’s Carrie Muskat writes. Of course, Lester was already familiar with Cubs president of baseball operations Theo Epstein from their time in Boston. “I think the Theo-Jon bromance was going to happen anyways,” says Hammel. “But [Lester] was definitely interested, and he was picking our brains all the time.” Here are more quick notes from the Central divisions.

Simon could move to the Tigers‘ bullpen if they re-sign Max Scherzer, Anthony Fenech of the Detroit Free Press suggests. Publicly, the Tigers won’t say that, Fenech writes, because they would look like they lost if Scherzer signed elsewhere. But it seems possible that the Tigers could be thinking of Simon primarily as a backup plan for their rotation.

The Indians‘ trade for Brandon Moss was a deal worth making, Terry Pluto of the Plain Dealer writes. Moss is expected to fully recover from offseason surgery, and the cost to get him (minor league second baseman Joey Wendle) wasn’t steep. With Moss in the fold, Pluto writes, the Indians will likely work to trade fellow lefty outfielder David Murphy, who has one year remaining before free agency.

Pluto also writes that the Indians dodged a bullet when Justin Masterson didn’t accept their three-year, $45MM extension offer last offseason. Masterson, of course, suffered through a year of injury and poor mechanics, and with him under contract, the Indians would have had about half their payroll committed to three players: Masterson, Michael Bourn and Nick Swisher. Masterson agreed to a one-year deal with the Red Sox this week.

The trust that Jon Lester has in Theo Epstein and Jed Hoyer from their days together in Boston is singled out by Yahoo Sports’ Jeff Passan as the key reason why the lefty chose Wrigley Field as his next home. Here’s some news from around the NL Central…

With Mat Latos and Alfredo Simon respectively traded to the Marlins and Tigers, Reds GM Walt Jocketty told reporters (including MLB.com’s Mark Sheldon) that the team can start to explore other upgrades now that they’ve addressed their payroll concerns. “We’re in a better position to start looking at some other possibilities to improve our club — the hitter we’re looking for and some bullpen depth,” Jocketty said. “We’re close to where we need to be, [payroll-wise]. Now we can concentrate on filling some of the needs.”

In an Insider-only post, ESPN’s Keith Law looks at the Reds‘ two pitching trades and feels the team got more from Detroit than they did from Miami. Law thinks Suarez is an improvement over Cozart and Jonathon Crawford could potentially be the Reds’ closer of the future.

The Orioles had preliminary discussions on a deal with the Pirates that would send Travis Snider to Baltimore for Brian Matusz, but there doesn’t seem to be much progress at the moment, according to Eduardo A. Encina of the Baltimore Sun (via Twitter).